US9345718B1 - Phospholipid ether analogs as cancer-targeting drug vehicles - Google Patents

Phospholipid ether analogs as cancer-targeting drug vehicles Download PDF

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US9345718B1
US9345718B1 US14/934,209 US201514934209A US9345718B1 US 9345718 B1 US9345718 B1 US 9345718B1 US 201514934209 A US201514934209 A US 201514934209A US 9345718 B1 US9345718 B1 US 9345718B1
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cancer
cells
clr1404
tumor
compound
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US20160136190A1 (en
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Jamey P. Weichert
Anatoly PINCHUK
Kevin Kozak
Marc LONGINO
Joseph Grudzinski
Benjamin Titz
Chorom Pak
Nathan Stehle
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Cellectar Biosciences Inc
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Cellectar Biosciences Inc
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Priority to US15/099,789 priority patent/US9480754B2/en
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Assigned to CELLECTAR BIOSCIENCES, INC. reassignment CELLECTAR BIOSCIENCES, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: PINCHUK, ANATOLY, GRUDZINSKI, JOSEPH, KOZAK, KEVIN, LONGINO, MARC, PAK, Chorom, STEHLE, NATHAN, TITZ, Benjamin, WEICHERT, JAMEY P.
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/548—Phosphates or phosphonates, e.g. bone-seeking
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/537—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines spiro-condensed or forming part of bridged ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/66—Phosphorus compounds
    • A61K31/665—Phosphorus compounds having oxygen as a ring hetero atom, e.g. fosfomycin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/543—Lipids, e.g. triglycerides; Polyamines, e.g. spermine or spermidine
    • A61K47/544—Phospholipids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/6551—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a four-membered ring
    • C07F9/65512—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a four-membered ring condensed with carbocyclic rings or carbocyclic ring systems

Definitions

  • W refers to an aryl, a C 1 -C 6 alkyl, an alkenyl, an optionally substituted C 3 -C 6 cycloalkyl and an optionally substituted C 3 -C 6 heterocycloalkyl.
  • linker compounds that are useful for the present invention include, but are not limited to, aminobutyramide, amino acids, glutaramic acids, dicarboxylic acids, carbamic acids, a carbonyl, 9,10-anthracenedicarboxylic acid, biphenyl-3,3′,5,5′-tetracarboxylic acid, biphenyl-3,4′,5-tricarboxylic acid, 5-bromoisophthalic acid, 5-cyano-1,3-benzenedicarboxylic acid, 2,2′-diamino-4,4′-stilbenedicarboxylic acid, 2,5-diaminoterephthalic acid, 2,5-dihydroxyterephthalic acid, 5-ethynyl-1,3-benzenedicarboxylic acid, 2-hydroxyterephthalic acid, imidazole, 2-methylimidazole, 2,6-naphthalenedicarboxylic acid, oxalic acid dehydrate, terephthalic acid, [1,1′:
  • linker compounds useful for the present invention also include, but are not limited to, lysosomal protease sensitive linkers with or without an aniline-based self-immolative fragment.
  • lysosomal protease sensitive linkers are examples of lysosomal protease sensitive linkers.
  • Actual dosage levels of active ingredients in the therapeutic compositions of this invention can be varied so as to obtain an amount of the active compound(s) which is effective to achieve the desired therapeutic response for a particular patient, compositions and mode of administration.
  • the selected dosage level will depend upon the activity of the particular compound, the route of administration, the severity of the condition being treated and the condition and prior medical history of the patient being treated. However, it is within the skill of the art to start doses of the compound at levels lower than required to achieve the desired therapeutic effect and to gradually increase the dosage until the desired effect is achieved.
  • the oral compositions may also include adjuvants such as wetting agents, emulsifying and suspending agents, sweetening, flavoring and perfuming agents.
  • adjuvants such as wetting agents, emulsifying and suspending agents, sweetening, flavoring and perfuming agents.
  • Examples 2 through 8 exhibit the ability of CLR1404 and related molecules to be sequestered and retained by various cancer types while simultaneously being eliminated from healthy tissue.
  • MDA-MB-468 cells a triple negative breast cancer cell line, were treated with CLR conjugates (CLR1601 and CLR1603) for 72 hours and with paclitaxel (“PTX”) for 24 hours. See Table 3.
  • MDA-MB-468 cells were also treated with CLR conjugates (CLR1606 and CLR1607) for 72 hours and with geldanamycin (“GEL”) for 48 hours. See Table 4.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Organic Chemistry (AREA)
  • Biophysics (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
US14/934,209 2014-11-17 2015-11-06 Phospholipid ether analogs as cancer-targeting drug vehicles Active US9345718B1 (en)

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US15/099,789 US9480754B2 (en) 2014-11-17 2016-04-15 Phospholipid ether analogs as cancer-targeting drug vehicles

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US14/934,209 US9345718B1 (en) 2014-11-17 2015-11-06 Phospholipid ether analogs as cancer-targeting drug vehicles

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US15/099,789 Active US9480754B2 (en) 2014-11-17 2016-04-15 Phospholipid ether analogs as cancer-targeting drug vehicles
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US15/894,430 Active US11439709B2 (en) 2014-11-17 2018-02-12 Phospholipid ether analogs as cancer-targeting drug vehicles

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US (4) US9345718B1 (es)
EP (2) EP3229810B1 (es)
JP (1) JP6832861B2 (es)
KR (1) KR102500181B1 (es)
CN (2) CN116655690A (es)
AU (1) AU2015350400B2 (es)
BR (1) BR112017010188B1 (es)
CA (1) CA2968145C (es)
DK (2) DK3750545T3 (es)
EA (1) EA037519B1 (es)
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IL (1) IL252102B (es)
MX (1) MX2017006382A (es)
PT (1) PT3229810T (es)
SG (1) SG11201703979QA (es)
SI (2) SI3229810T1 (es)
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US20160136290A1 (en) * 2014-11-17 2016-05-19 Cellectar Biosciences, Inc. Phospholipid Ether Analogs as Cancer-Targeting Drug Vehicles
US10287353B2 (en) 2016-05-11 2019-05-14 Huya Bioscience International, Llc Combination therapies of HDAC inhibitors and PD-1 inhibitors
US10385131B2 (en) 2016-05-11 2019-08-20 Huya Bioscience International, Llc Combination therapies of HDAC inhibitors and PD-L1 inhibitors
US11013720B2 (en) 2019-05-24 2021-05-25 National Chiao Tung University Ganetespib-containing particle, pharmaceutical composition comprising the same, and their use in anticancer treatment

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JP2021512622A (ja) * 2018-02-06 2021-05-20 シアトル チルドレンズ ホスピタル ディー／ビー／エー シアトル チルドレンズ リサーチ インスティテュート フルオレセイン結合エーテルリン脂質（ｆｌ−ｐｌｅ）で標識された腫瘍に対して最適なｔ細胞機能を示すフルオレセイン特異的ｃａｒ
JP7402172B2 (ja) * 2018-04-10 2023-12-20 セレクター・バイオサイエンシズ・インコーポレイテッド リン脂質－フラバグリン複合体およびそれを標的癌治療に使用する方法
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AU2020346898A1 (en) 2019-09-12 2022-04-07 Cellectar Biosciences, Inc. Phospholipid ether conjugates as cancer-targeting drug vehicles
BR112022006739B1 (pt) * 2019-10-10 2024-01-23 Cellectar Biosciences, Inc Conjugados fosfolipídio-flavagina e métodos de uso do mesmo para terapia direcionada a câncer
CN114437128B (zh) * 2022-01-28 2023-12-19 中国科学院长春应用化学研究所 一种胆碱磷酸修饰的紫杉醇药物及其制备方法和应用

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US20160228564A1 (en) * 2014-11-17 2016-08-11 Cellectar Biosciences, Inc. Phospholipid Ether Analogs as Cancer-Targeting Drug Vehicles
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